Convergent synthesis of N-linked glycopeptides on a solid support

Solid-supported synthesis can be conducted to produce a variety of glycopeptides in good overall yields. The carbohydrates are formed by the glycal assembly method. The polymer-bound construct terminates in a glycal. The terminal double bond can be functionalized to provide a C2-N-acetyl glucosamine linkage with an amino group in the anomeric position. The latter can be coupled, in a convergent manner, to the gamma-carboxyl group of an aspartyl residue on a preformed peptide. Iodosulfonamidation of the polymer-bound glucal to the N-acetyl glucosamine using anthracenesulfonamide was crucial for the success of the solid-phase synthesis. This general method was employed in the formation of a variety of glycopeptides.